DENNIS GILBERT
Rod Dedeaux Lifetime Achievement Award
Dennis Gilbert is a prominent figure in the insurance and sports industries, known for his successful careers as both an insurance and sports agent, as well as his philanthropic work.
Raised in Gardena, California, Gilbert began his career as a baseball player in the Boston Red Sox organization, then entered the insurance industry in the early 1970s. He quickly established himself as a successful insurance agent. Then, eight years later, he diversified and became a sports agent as well. His dedication to his work and commitment to providing exceptional service led to a rapid rise through the ranks of both industries and he soon became one of the most respected insurance & sports agents in the country, representing players such as: Barry Bonds, Bobby Bonilla, Mike Piazza, George Brett, Ricky Henderson, to name a few. In broadcasting, he represented two icons: Larry King and Vin Scully. His keen eye for talent and deep understanding of the sports world made him a sought‐after advisor.
In 2000, he sold his interest in the sports agency, and two years later, joined the Chicago White Sox as special assistant to the chairman, Jerry Reinsdorf. Throughout his career, Gilbert has been an active philanthropist and supporter of various charitable causes. Dennis was instrumental in creating the Dennis Gilbert Field at Southwest College. He founded the Professional Baseball Foundation, which merged with the MLB Baseball Assistance Program. In 2006, he was awarded their humanitarian award and in 2022 he received their lifetime achievement award. He was also awarded man of the year by the Anti‐Defamation League and a recipient of the lifetime achievement award by both Gardena high school and Los Angeles City College. He has been recognized for his generous contributions to organizations that support cancer research, education, and other important causes. He supports St. Jude’s Children’s Research Hospital and the Children’s Hospital of Los Angeles. Gilbert has been recognized with many insurance industry awards and honors, including Man of the Year Awards multiple times with Equitable, Nationwide and Provident Mutual. He was also the recipient of the 2018 Insurance America Awards for excellence in community service, which recognizes insurance professionals and those who make significant contributions to their communities through volunteer work and philanthropy. Additionally, he has been recognized by the National Association of Insurance and Financial Advisers for his outstanding commitment to serving his clients and the community.
Outside of his work and philanthropic endeavors, Gilbert is a devoted family man. He has been married forty‐five years, to the love of his life, Cindi Gilbert, and together they have three daughters, two son‐inlaw‘ s and two grandchildren. His family is a constant source of inspiration and support, and he considers them to be his greatest achievement in life.
Overall, Dennis Gilbert's career as an insurance agent, a sports agent, being special assistant to Jerry Reinsdorf and his dedication to philanthropy, have all earned him a well‐deserved reputation as one of the most respected and admired figures in the world of business and sports.